Dentigerous cysts are the most common developmental cysts of the jaws, most frequently associated with impacted mandibular third molar teeth. Dentigerous cysts around supernumerary teeth, however, account for 5% of all dentigerous cysts, with most developing around a mesiodens in the anterior maxilla. This report describes two cases of a dentigerous cyst associated with an impacted mesiodens. Both of the patients complained of swelling in the maxillary anterior region. Radiographic examination revealed an impacted mesiodens surrounded by a large corticated radiolucency in both cases. A provisional diagnosis of infected odontogenic cyst was made. The cysts were enucleated with the removal of the mesiodens in the two cases. Histopathological examination confirmed the diagnosis of infected dentigerous cyst associated with an impacted mesiodens in both cases. The patients remained asymptomatic, and no complications were noted.